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English pro­fessor Benedict Whalen traveled Italy while jug­gling. Benedict Whalen | Courtesy

There are two ways to tour Rome: the normal way, and the slightly more extra­or­dinary — where you bring jug­gling pins instead of cash, survive on bread, cheese, and olives, and make your parents fear you’ll never return.

“We wanted to see Europe,” Pro­fessor of English Benedict Whalen said, “but there was also a com­ponent of prayer and vis­iting churches and relying upon charity in a sense, so we didn’t take money.”

Instead, Whalen and 11 of his high school friends from boarding school per­formed for people on the street. Whalen accom­panied the group with guitar, bodhrán — an Irish drum — and singing, while his friends juggled every­thing from balls and pins, to knives and flaming torches. Later on, a bagpipe player also joined them.

“Our time was divided each day between putting on shows to get enough money for lunch and then stopping at a church for mass and then going back out and doing shows all afternoon until we said, ‘Ok, we earned enough for dinner and a hostel for the night.’”

Whalen, who had just grad­uated from Gregory the Great Academy in north­eastern Penn­syl­vania said the hardest part in planning the trip was con­vincing his parents to let him go. His father, Hillsdale College Provost David Whalen, ended up giving him per­mission, but only if the group brought suf­fi­cient emer­gency funds to eat and sleep, and if there was an adult to supervise. Ben Whalen said the adult was a college student, and the troupe never used any emer­gency cash on the trip.  

“We went hungry several nights,” Whalen said. “We made enough to get a couple loaves of bread and some cheese or some­thing, but it was not a real dinner.”

For­tu­nately, they never slept on the streets, but there was always a chance that they would.

One par­ticular night after they had secured two rooms at a hostel, they met two female British tourists who had somehow lost their room and appeared very dis­tressed. The group decided to help by giving up one of their rooms.

“I dis­tinctly remember that,” he said. “We 12 guys piled on top of each other in out­ra­geously cramped cir­cum­stances in our one room. But you know you also felt that because we were, in a sense, living on charity or whatever people wanted to give us, we were passing that on to others in need, and so it was fitting in the spirit of the thing.”  

Besides the chal­lenges of affording daily meals and hotels, no one in the group spoke Italian. But having some level of expe­rience in Latin at school back in the U.S., the troupe members were able to com­mu­nicate somewhat with Italians and ask for direc­tions.

“They would look at us sort of funnily and have some idea of what we were saying, and I think the shared ety­mology of the lan­guages was a help there,” Whalen said.

On the last day of the trip, Whalen’s parents almost realized their worst fears. With an evening flight heading back to the states that night, the troupe was putting on its last show in one of the piazzas they found to be more suc­cessful, because it was a heavier tourist area. But before they could pass around the hats, three men came around the building.  “They were dressed in black with caps — like a director’s caps or some­thing like that — and ear­pieces in, and they looked very serious…It turned out there was a director of ‘Ocean’s Twelve’ who was filming a couple blocks away, and we were making too much noise, and the actors were having trouble getting into char­acter.”

Whalen’s troupe responded that they had to put on the show because they had no other way to get to the airport that evening.

“He said, ‘How much do you need?’ And we said whatever amount it was — you know, maybe 60 euros or some­thing more — and he just pulled out a huge wad of cash and paid us exactly what we needed.”

Whalen said the group was amused afterward that they had actually been paid to stop per­forming.

“It was also funny because we realized we probably could have asked him for much more than we did, but we were young and naïve…That was our great moment: inter­rupting Brad Pitt and ‘Ocean’s Twelve.’”

Provost Whalen agreed that the troupe should have taken advantage of the sit­u­ation.

“I think they bungled it,” he said. “You double the amount, triple it…You say, ‘We want signed 8.5x11” colored glossies of these three stars who were in the movie’…You try to finagle a day on the set watching them: ‘We’ll shut up if we can watch and if you pay us so we don’t have to starve tonight.’ ‘Do you need some extras for the film? We’d be happy to walk by. In fact, I think you need a little scene where a juggler is doing some stuff on the street corner.’”

Whalen still keeps in touch with some of the people on the trip and remarks that the trip was a “strange” albeit for­mative expe­rience for him.

“It was my first real intro­duction to Rome,” he said. “I later as a college student spent a semester studying in Rome. It was also important for your imag­i­native engagement and under­standing of the church and Europe, the old world. And it was important sharing that with these fellow boys, and espe­cially as many of us were heading off to a diverse number of col­leges.”

Despite the risks involved, Provost Whalen said one can’t deprive high school and college stu­dents of adventure.

“You can put bound­aries around things, but they always need a fun­da­mental contest with reality,” he said. “That age needs adventure.”